Enantio- and Diastereoselective Two-Pot Synthesis of Isoquinuclidines from Glutaraldehyde and N-Aryl Imines with DFT Calculations.
J Org Chem
; 84(19): 12408-12419, 2019 10 04.
Article
en En
| MEDLINE
| ID: mdl-31486644
ABSTRACT
A pot-economic method for the enantio- and diastereoselective synthesis of a [2.2.2] azabicyclic isoquinuclidine system is developed. This protocol involves the proline-catalyzed direct Mannich reaction-cyclization/IBX-mediated site-selective oxidation/NaBH4-reduction sequence between glutaraldehyde and imines to generate in situ chiral 1,2-DHPs, followed by the diastereoselective Diels-Alder reaction with N-aryl maleimides furnishing isoquinuclidines in overall five steps. A variety of isoquinuclidines having five-contiguous chiral centers, including an all-carbon quaternary, were prepared with high yields (up to 78%) and excellent stereoselectivity (>501 dr, and up to >991 er). DFT calculations support the observed high stereoselective reaction outcome.
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Banco de datos:
MEDLINE
Idioma:
En
Revista:
J Org Chem
Año:
2019
Tipo del documento:
Article
País de afiliación:
India